Potassium Carbonate → HCID 69372083, compound

HRID 2213744Notes

Reaction equation

HRID 2213744 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[CH:7]=[C:8]3[NH:31][CH:30]=[N:29][C:9]3=[CH:10][C:11]=2[C:12]=1[N:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)C=O)#[N:2].C(=O)([O-])[O-].[K+].[K+]>CO>[O:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:13][C:12]2[C:11]3[CH:10]=[C:9]4[N:29]=[CH:30][N:31]=[C:8]4[CH2:7][C:6]=3[N:5]=[CH:4][C:3]=2[C:1]#[N:2])=[CH:17][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178510286HCID 178510286, compound

Product 1

HCID 69372083HCID 69372083, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 211.8 mg (0.52 mmol) of 7-cyano-3H-imidazo[4,5-g]quinolin-8-yl(4-phenoxyphenyl)formamide and 288.9 mg (2.09 mmol) of potassium carbonate in 15 mL of methanol is refluxed for 2.5 hours. The solution is concentrated and the residue is diluted with water followed by neutralization to pH 7–8 with acetic acid. The precipitate is collected by filtration and washed with water and dried in vacuo, giving a deep yellow solid. The solid is purified by flash chromatography (elution with a gradient of 98:2 to 90:10 methylene chloride/methanol) yields 137.4 mg (70.0%) of the final product as a yellow solid, mp>270° C.

Workup

  1. temperatureis refluxed for 2.5 hours
  2. concentrationThe solution is concentrated
  3. additionthe residue is diluted with water
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. customgiving a deep yellow solid
  8. customThe solid is purified by flash chromatography (
  9. washelution with a gradient of 98:2 to 90:10 methylene chloride/methanol)

Sources & evidence

ORD record
ord-a3f33270a40044178a5e3e10f1d03cd9
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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